新型香豆素类Mannich碱荧光功能化合物的合成及性质研究  

Synthesis and Properties of Novel Coumarin-Based Mannich Base Fluorescent Functional Compounds

作　　者：杨栋[1,2] 郭媛[1,2] 陈康裕[1,2] 彭梦姣[1,2] 安静 

机构地区：[1]西北大学化学与材料科学学院 [2]西北大学合成与天然功能分子化学教育部重点实验室,西安710069

出　　处：《有机化学》2011年第8期1277-1281,共5页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21072158);陕西省教育厅专项基金(No.09JK750);西北大学研究生交叉学科基金(No.09YJC21)资助项目

摘　　要：以4-卤代间苯二酚为原料经甲酰化反应合成了2,4-二羟基-5-卤代苯甲醛,再通过Knoevenagel缩合反应合成了5种香豆素衍生物,最后经Mannich反应获得了5种未见文献报道的香豆素类荧光功能化合物.所得的荧光化合物的结构均用1H NMR,IR,MS和元素分析等方法进行了表征,并且对该类化合物的荧光性质及对金属离子的响应进行了研究.结果发现,由于光诱导电子转移(PET)的作用,在Mannich反应后,目标产物的荧光强度弱于反应前,而当该产物与金属离子配合后,PET作用减弱,荧光强度得到恢复.2,4-Dihydroxy-5-halobenzaldehydes were synthesized by using 4-haloresorcinol as the raw ma- terial via formylation reaction. Then five coumarin derivatives were prepared via Knoevenagel condensation reaction. Finally, five coumarin functional derivatives which have not been reported were obtained via Man- nich reaction. The structures of the products were characterized by 1H NMR, IR, MS techniques and ele- mental analyses. The fluorescent properties and response to metal cations of these fluorescent compounds were studied. Because of photoinduced electron transfer （PET） effect, the fluorescent intensity of the cou- marin functional derivatives obtained by Mannich reaction decreased. When the metal ions were combined with the above functional compounds, the fluorescent intensity of the compounds was enhanced due to weakening of PET effect.

关 键 词：香豆素类Mannich碱 荧光功能化合物 金属离子 合成 

分 类 号：O629.3[理学—有机化学]